This invention relates to certain cyclic amides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use as fungicides.
The control of plant diseases caused by fungal plant pathogens is extremely important in achieving high crop efficiency. Plant disease damage to ornamental, vegetable, field, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
WO 94/11334 discloses certain amides and esters of Formula i as fungicides ##STR2## wherein n is 0-4;
X is CHOCH.sub.3, CHCH.sub.3, or NOCH.sub.3 ; PA1 Y is O or NH; PA1 R.sup.1 is, among others, nitro; cyano; halogen; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.4 alkoxy; C.sub.1 -C.sub.4 haloalkoxy; or C.sub.1 -C.sub.4 alkylthio; PA1 R.sup.2 is, among others, nitro, cyano, halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylcarbonylanrino, or C.sub.1 -C.sub.4 alkoxycarbonylamino; PA1 R.sup.3 is, among others, R.sup.4 --T--C(.dbd.Z.sup.1)-- or R.sup.5 --C(.dbd.Z.sup.2)--; PA1 Z.sup.1 is, among others, O or S; PA1 Z.sup.2 is, among others, O or S; and PA1 T is, among others, O, S, or NR.sup.7 ; and PA1 R.sup.2 is OR.sup.5 or NHR.sup.6 ; PA1 R.sup.3 is C.sub.3 -C.sub.8 cycloalkyl; PA1 R.sup.4 is, among others, C.sub.1 -C.sub.10 alkoxy, C.sub.2 -C.sub.7 alkoxycarbonyl, halogen, cyano, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 haloalkyl; PA1 R.sup.5 and R.sup.6 are C.sub.1 -C.sub.6 alkyl; and PA1 n is 0-5. PA1 A is O; S; N; NR.sup.5 ; or CR.sup.14 ; PA1 G is C or N; provided that when G is C, then A is O, S or NR.sup.5 and the floating double bond is attached to G; and when G is N, then A is N or CR.sup.14 and the floating double bond is attached to A; PA1 W is O; S; NH; N(C.sub.1 -C.sub.6 alkyl); or NO(C.sub.1 -C.sub.6 alkyl); PA1 X is OR.sup.1 ; S(O).sub.m R.sup.1 ; or halogen; PA1 R.sup.1 is C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.2 -C.sub.4 alkylcarbonyl; or C.sub.2 -C.sub.4 alkoxycarbonyl; PA1 R.sup.2 is H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.4 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.2 -C.sub.4 alkylcarbonyl; C.sub.2 -C.sub.4 alkoxycarbonyl; hydroxy; C.sub.1 -C.sub.2 alkoxy; or acetyloxy; PA1 R.sup.3 and R.sup.4 are each independently halogen; cyano; nitro; hydroxy; C.sub.1 --C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.2 -C.sub.6 alkenyloxy; C.sub.2 -C.sub.6 alkynyloxy; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 alkylsulfinyl; C.sub.1 -C.sub.6 alkylsulfonyl; formyl; C.sub.2 -C.sub.6 alkylcarbonyl; C.sub.2 -C.sub.6 alkoxycarbonyl; NH.sub.2 C(O); (C.sub.1 -C.sub.4 alkyl)NHC(O); (C.sub.1 -C.sub.4 alkyl).sub.2 NC(O); Si(R.sup.25).sub.3 ; Ge(R.sup.25).sub.3 ; (R.sup.25).sub.3 Si--C.tbd.C--; or phenyl, phenylethynyl, benzoyl, or phenylsulfonyl each substituted with R.sup.8 and optionally substituted with one or more R.sup.10 ; or PA1 when R.sup.3 and R.sup.4 are attached to adjacent atoms, R.sup.3 and R.sup.4 can be taken together as C.sub.3 -C.sub.5 alkylene, C.sub.3 -C.sub.5 haloalkylene, C.sub.3 -C.sub.5 alkenylene or C.sub.3 -C.sub.5 haloalkenylene each optionally substituted with 1-2 C.sub.1 -C.sub.3 alkyl; PA1 R.sup.5 is H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.2 -C.sub.4 alkylcarbonyl; or C.sub.2 -C.sub.4 alkoxycarbonyl; PA1 Y is --NR.sup.15 --; --C(.dbd.O)--; --CHR.sup.15 OC(.dbd.S)N(R.sup.15)--; --CHR.sup.15 OC(.dbd.O)O--; --CHR.sup.15 OC(.dbd.S)O--; --CHR.sup.15 OC(.dbd.O)S--; --CHR.sup.15 OC(.dbd.S)S--; --CHR.sup.15 SC(.dbd.O)N(R.sup.15)--; --CHR.sup.15 SC(.dbd.S)N(R.sup.15)--; --CHR.sup.15 SC(.dbd.O)O--; --CHR.sup.15 SC(.dbd.S)O--; --CHR.sup.15 SC(.dbd.O)S--; --CHR.sup.15 SC(.dbd.S)S--; --CHR.sup.15 SC(.dbd.NR.sup.15)S--; --CHR.sup.15 N(R.sup.15)C(.dbd.O)N(R.sup.15)--; --CHR.sup.15 O--N(R.sup.15)C(.dbd.O)N(R.sup.15)--; --CHR.sup.15 O--N(R.sup.15)C(.dbd.S)N(R.sup.15)--; --CHR.sup.15 O--N.dbd.C(R.sup.7)NR.sup.15 --; --CHR.sup.15 O--N.dbd.C(R.sup.7)OCH.sub.2 --; --CHR.sup.15 O--N.dbd.C(R.sup.7)--N.dbd.N--; --CHR.sup.15 O--N.dbd.C(R.sup.7)--C(.dbd.O)--; --CHR.sup.15 O--N.dbd.C(R.sup.7)--C(.dbd.N--A.sup.2 --Z.sup.1)--A.sup.1 --; --CHR.sup.15 O--N.dbd.C(R.sup.7)--C(R.sup.7).dbd.N--A.sup.2 --A.sup.3 --; --CHR.sup.15 O--N.dbd.C(--C(R.sup.7).dbd.N--A.sup.2 --Z.sup.1)--; --CHR.sup.15 O--N.dbd.C(R.sup.7)--CH.sub.2 O--; --CHR.sup.15 O--N.dbd.C(R.sup.7)--CH.sub.2 S--; --O--CH.sub.2 CH.sub.2 O--N.dbd.C(R.sup.7)--; --CHR.sup.15 O--C(R.sup.7).dbd.N--; --CHR.sup.15 S--C(R.sup.7).dbd.N--; --C(R.sup.7).dbd.N--NR.sup.15 --; --CH.dbd.N--N.dbd.C(R.sup.7)--; --CHR.sup.15 N(R.sup.15)--N.dbd.C(R.sup.7)--; --CHR .sup.15 N(COCH.sub.3)--N.dbd.C(R.sup.7)--; --OC(.dbd.S)NR.sup.15 C(.dbd.O)--; --CHR.sup.6 --C(.dbd.W.sup.1)--A.sup.1 --; --CHR.sup.6 CHR.sup.6 --C(.dbd.W.sup.1)--A.sup.1 --; --CR.sup.6 .dbd.CR.sup.6 --C(.dbd.W.sup.1)--A.sup.1 --; --C.tbd.C--C(.dbd.W.sup.1)--A.sup.1 --; --N.dbd.CR.sup.6 --C(.dbd.W.sup.1)--A.sup.1 --; --CH(OR.sup.26)--; --CHR.sup.27 --; --CHR.sup.6 CHR.sup.28 --; --CHR.sup.28 CHR.sup.6 --; --CR.sup.6 .dbd.CR.sup.29 --; --CR.sup.29 .dbd.CR.sup.6 --; --CHR.sup.30 O--; --OCHR.sup.30 --; --CHR.sup.30 S(O).sub.n --; --S(O).sub.n CHR.sup.30 --; --CHR.sup.30 O--N.dbd.C(R.sup.7)--; --CHR.sup.15 O--N.dbd.C(R.sup.31)--; --(R.sup.7)C.dbd.N--OCH(R.sup.30)--; --(R.sup.31)C.dbd.N--OCH(R.sup.15)--; --C(R.sup.31).dbd.N--O--; --O--N.dbd.C(R.sup.31 )--; --CHR.sup.30 OC(.dbd.O)N(R.sup.15)--; or --CHR.sup.15 OC(.dbd.O)N(R.sup.32)--; and the directionality of the Y linkage is defined such that the moiety depicted on the left side of the linkage is bonded to E and the moiety on the right side of the linkage is bonded to Z; PA1 Z.sup.1 is H or --A.sup.3 --Z; PA1 W.sup.1 is O or S; PA1 A.sup.1 is O; S; NR.sup.15 ; or a direct bond; PA1 A.sup.2 is O; NR.sup.15 ; or a direct bond; PA1 A.sup.3 is --C(.dbd.O)--; --S(O).sub.2 --; or a direct bond; PA1 each R.sup.6 is independently H; 1-2 CH.sub.3 ; C.sub.2 -C.sub.3 alkyl; C.sub.1 -C.sub.3 alkoxy; C.sub.3 -C.sub.6 cycloalkyl; formylamino; C.sub.2 -C.sub.4 alkylcarbonylamino; C.sub.2 -C.sub.4 alkoxycarbonylamino; NH.sub.2 C(O)NH; (C.sub.1 -C.sub.3 alkyl)NHC(O)NH; (C.sub.1 -C.sub.3 alkyl).sub.2 NC(O)NH; N(C.sub.1 -C.sub.3 alkyl).sub.2 ; piperidinyl; morpholinyl; 1-2 halogen; cyano; or nitro; PA1 each R.sup.7 is independently H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 alkylsulfinyl; C.sub.1 -C.sub.6 alkylsulfonyl; C.sub.1 -C.sub.6 haloalkylthio; C.sub.1 -C.sub.6 haloalkylsulfinyl; C.sub.1 -C.sub.6 haloalkylsulfonyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.2 -C.sub.4 alkylcarbonyl; C.sub.2 -C.sub.4 alkoxycarbonyl; halogen; cyano; nitro; hydroxy; amino; NH(C.sub.1 -C.sub.6 alkyl); N(C.sub.1 -C.sub.6 alkyl)2; or morpholinyl; PA1 each Z is independently selected from: PA1 v) adamantyl substituted with R.sup.9 and optionally substituted with one or more R.sup.10 ; PA1 each Q is independently selected from the group --CHR.sup.13 --, --NR13--, --O--, and --S(O).sub.p --; PA1 R.sup.8 is H; 1-2 halogen; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 haloalkylthio; C.sub.1 -C.sub.6 alkylsulfinyl; C.sub.1 -C.sub.6 alkylsulfonyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.3 -C.sub.6 alkenyloxy; CO.sub.2 (C.sub.1 -C.sub.6 alkyl); NH(C.sub.1 -C.sub.6 alkyl); N(C.sub.1 -C.sub.6 alkyl).sub.2 ; cyano; nitro; SiR.sup.19 R.sup.20 R.sup.21 ; or GeR.sup.19 R.sup.20 R.sup.21 ; PA1 R.sup.9 is H; 1-2 halogen; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 haloalkylthio; C.sub.1 -C.sub.6 alkylsulfinyl; C.sub.1 -C.sub.6 alkylsulfonyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.3 -C.sub.6 alkenyloxy; CO.sub.2 (C.sub.1 -C.sub.6 alkyl); NH(C.sub.1 -C.sub.6 alkyl); N(C.sub.1 -C.sub.6 alkyl).sub.2 ; --C(R.sup.18).dbd.NOR.sup.17 ; cyano; nitro; SF.sub.5 ; SiR.sup.22 R.sup.23 R.sup.24 ; or GeR.sup.22 R.sup.23 R.sup.24 ; or R.sup.9 is phenyl, benzyl, benzoyl, phenoxy, pyridinyl, pyridinyloxy, thienyl, thienyloxy, furanyl, pyrimidinyl, or pyrimidinyloxy each optionally substituted with one of R.sup.11, R.sup.12, or both R.sup.11 and R.sup.12 ; PA1 each R.sup.10 is independently halogen; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.4 alkoxy; nitro; or cyano; or PA1 when R.sup.9 and an R.sup.10 are attached to adjacent atoms on Z, R.sup.9 and said adjacently attached R.sup.10 can be taken together as --OCH.sub.2 O-- or --OCH.sub.2 CH.sub.2 O--; each CH.sub.2 group of said taken together R.sup.9 and R.sup.10 optionally substituted with 1-2 halogen; or PA1 when Y and an R.sup.10 are attached to adjacent atoms on Z and Y is PA1 J is --CH.sub.2 --; --CH.sub.2 CH.sub.2 --; --OCH.sub.2 --; --CH.sub.2 O--; --SCH.sub.2 --; --CH.sub.2 S--; --N(R.sup.16)CH.sub.2 --; or PA1 R.sup.11 and R.sup.12 are each independently halogen; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.4 alkoxy; C.sub.1 -C.sub.4 haloalkoxy; nitro; cyano; Si(R.sup.25).sub.3 ; or Ge(R.sup.25).sub.3 ; PA1 each R.sup.13 is independently H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; or phenyl optionally substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano; PA1 R.sup.14 is H; halogen; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; or C.sub.3 -C.sub.6 cycloalkyl; PA1 each R.sup.15 is independently H; C.sub.1 -C.sub.3 alkyl; C.sub.3 -C.sub.6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano; or PA1 when Y is --CHR.sup.15 N(R.sup.15)C(.dbd.O)N(R.sup.15)--, the two R.sup.15 attached to nitrogen atoms on said group can be taken together as --(CH.sub.2).sub.s --; or PA1 when Y is --CHR.sup.15 O--N.dbd.C(R.sup.7)NR.sup.15 --, R.sup.7 and the adjacently attached R.sup.15 can be taken together as --CH.sub.2 --(CH.sub.2).sub.s --; --O--(CH.sub.2).sub.s --; --S--(CH.sub.2).sub.s --; or PA1 R.sup.16, R.sup.17, and R.sup.18 are each independently H; C.sub.1 -C.sub.3 alkyl; C.sub.3 -C.sub.6 cycloalkyl; or phenyl optionally substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano; PA1 R.sup.19, R.sup.20, R.sup.21, R.sup.22, R.sup.23, and R.sup.24 are each independently C.sub.1 -C.sub.6 alkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.1 -C.sub.4 alkoxy; or phenyl; PA1 each R.sup.25 is independently C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 haloalkyl; C.sub.2 -C.sub.4 alkenyl; C.sub.1-C.sub.4 alkoxy; or phenyl; PA1 R.sup.26 is H; C.sub.1 -C.sub.3 alkyl; C.sub.3 -C.sub.6 cycloalkyl; or phenyl optionally substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano; PA1 R.sup.27 and R.sup.28 are each independently C.sub.1 -C.sub.3 alkoxy; C.sub.3 -C.sub.6 cycloalkyl; formylamino; C.sub.2 -C.sub.4 alkylcarbonylamino; C.sub.2 -C.sub.4 alkoxycarbonylarnino; NH.sub.2 C(O)NH; (C.sub.1 -C.sub.3 alkyl)NHC(O)NH; (C.sub.1 -C.sub.3 alkyl).sub.2 NC(O)NH; N(C.sub.1 -C.sub.3 alkyl).sub.2 ; piperidinyl; morpholinyl; cyano; or nitro; PA1 R.sup.29 is C.sub.1 -C.sub.3 alkoxy; C.sub.3 -C.sub.6 cycloalkyl; formylamino; C.sub.2 -C.sub.4 alkylcarbonylamino; C.sub.2 -C.sub.4 alkoxycarbonylamino; NH.sub.2 C(O)NH; (C.sub.1 -C.sub.3 alkyl)NHC(O)NH; (C.sub.1 -C.sub.3 alkyl).sub.2 NC(O)NH; N(C.sub.1 -C.sub.3 alkyl)2; piperidinyl; morpholinyl; halogen; cyano; or nitro; PA1 R.sup.30 is C.sub.3 -C.sub.6 cycloalkyl; or phenyl optionally substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano; R.sup.31 is C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 alkylsulfinyl; C.sub.1 -C.sub.6 alkylsulfonyl; C.sub.1 -C.sub.6 haloalkylthio; C.sub.1 -C.sub.6 haloalkylsulfinyl; C.sub.1 -C.sub.6 haloalkylsulfonyl; nitro; hydroxy; amino; NH(C.sub.1 -C.sub.6 alkyl); N(C.sub.1 -C.sub.6 alkyl).sub.2 ; or halogen; PA1 R.sup.32 is C.sub.3 -C.sub.6 cycloalkyl; PA1 m, n and p are each independently 0, 1 or 2; PA1 r is 0 or 1; and PA1 s is 2 or 3; PA1 i) when Y is --CH(OR.sup.26)--, --CHR.sup.27 --, --CHR.sup.6 CHR.sup.28 --, --CHR.sup.28 CHR.sup.6 --, --OCHR.sup.30 --, --S(O).sub.n CHR.sup.30 -- or --(R.sup.7)C.dbd.N--OCH(R.sup.30)-- and Z is C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, or C.sub.2 -C.sub.10 alkynyl each substituted with R.sup.9 and optionally substituted with one or more R.sup.10, then R.sup.9 is other than H, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, or C.sub.2 -C.sub.6 alkynyl; PA1 ii) when Y is --CR.sup.6 .dbd.CR.sup.29 -- or --CR.sup.29 .dbd.CR.sup.6 -- and Z is C.sub.1 -C.sub.10 alkyl or C.sub.2 -C.sub.10 alkenyl each substituted with R.sup.9 and optionally substituted with one or more R.sup.10, then R.sup.9 is other than H, 1-2 halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, or C.sub.2 -C.sub.6 haloalkenyl; PA1 iii) when Y is --NR.sup.15 --, R.sup.15 is H or C.sub.1 -C.sub.3 alkyl, and R.sup.9 is SiR.sup.22 R.sup.23 R.sup.24 or GeR.sup.22 R.sup.23 R.sup.24, then Z is other than phenyl or a 5 to 14-membered aromatic heterocyclic ring system each substituted with R.sup.9 and optionally substituted with one or more R.sup.10 ; PA1 iv) when Y is --C(.dbd.O)-- and R.sup.9 is SiR.sup.22 R.sup.23 R.sup.24 or GeR.sup.22 R.sup.23 R.sup.24, then Z is other than phenyl or a 5 to 14-membered aromatic heterocyclic ring system each substituted with R.sup.9 and optionally substituted with one or more R.sup.10 ; PA1 v) when Y is --CH(OR.sup.26)--, R.sup.26 is H or C.sub.1 -C.sub.3 alkyl, and R.sup.9 is SiR.sup.22 R.sup.23 R.sup.24 or GeR.sup.22 R.sup.23 R.sup.24, then Z is other than phenyl or a 5 to 14-membered aromatic heterocyclic ring system each substituted with R.sup.9 and optionally substituted with one or more R.sup.10 ; PA1 vi) when Y is --NR.sup.15 -- and R.sup.15 is H or C.sub.1 -C.sub.3 alkyl, then Z is other than PA1 vii) when Y is --CHR.sup.15 O--N.dbd.C(R.sup.31)-- or --(R.sup.31)C.dbd.N--OCH(R.sup.15)--, R.sup.15 is H or C.sub.1 -C.sub.3 alkyl and R.sup.31 is C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, C.sub.1 -C.sub.6 haloalkylthio, C.sub.1 -C.sub.6 haloalkylsulfinyl, C.sub.1 -C.sub.6 haloalkylsulfonyl or halogen, then Z is other than PA1 viii) when Y is --C(.dbd.O)--, then Z is other than PA1 ix) when Y is --C(R.sup.31).dbd.N--O-- or --O--N.dbd.C(R.sup.31)-- and R.sup.31 is C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, C.sub.1 -C.sub.6 haloalkylthio, C.sub.1 -C.sub.6 haloalkylsulfinyl, C.sub.1 -C.sub.6 haloalkylsulfonyl or halogen, then Z is other than PA1 x) when Y is --CH(OR.sup.26)-- and R.sup.26 is H or C.sub.1 -C.sub.3 alkyl, then Z is other than PA1 suitable salts thereof, wherein: PA1 R.sup.9 is H; 1-2 halogen; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.1 -C.sub.6 alkylthio; cyano; CO.sub.2 (C.sub.1 -C.sub.6 alkyl); NH(C.sub.1 -C.sub.6 alkyl); N(C.sub.1 -C.sub.6 alkyl).sub.2 ; SiR.sup.22 R.sup.23 R.sup.24 ; or GeR.sup.22 R.sup.23 R.sup.24 ; or R.sup.9 is C.sub.3 -C.sub.6 cycloalkyl, phenyl, phenoxy, pyridinyl, pyridinyloxy, pyrimidinyl, or pyrimidinyloxy, each optionally substituted with one of R.sup.11, R.sup.12, or both R.sup.11 and R.sup.12 ; and PA1 R.sup.30 is C.sub.3 -C.sub.6 cycloalkyl. PA1 Z is selected from the group phenyl; pyridinyl; pyrimidinyl; and naphthalenyl; each group substituted with R.sup.9 and optionally substituted with one or more R.sup.10 ; and PA1 R.sup.7 is H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 alkylthio; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 alkynyl; cyclopropyl; halogen; or cyano. PA1 A is O; N; NR5; or CR.sup.14 ; PA1 X is OR.sup.1 ; PA1 R.sup.1 is C.sub.1 -C.sub.3 alkyl; PA1 R.sup.2 is H or C.sub.1 -C.sub.2 alkyl; PA1 Y is --CH.sub.2 S--C(R.sup.7).dbd.N--; --CH.dbd.CR.sup.6 --C(.dbd.W.sup.1)--A.sup.1 --; --CH.sub.2 O--N.dbd.C(R.sup.31)--; or --(R.sup.7)C.dbd.N--OCH(R.sup.30)--; PA1 R.sup.7 is H; C.sub.1 -C.sub.3 alkyl; C.sub.1 -C.sub.3 haloalkyl; C.sub.1 -C.sub.3 alkoxy; C.sub.1 -C.sub.3 alkylthio; or cyclopropyl; and PA1 R.sup.30 is cyclopropyl. PA1 A is O or NR.sup.5 ; PA1 G is C; and PA1 Y is --CH.dbd.CR.sup.6 --C(.dbd.W.sup.1)--A.sup.1 --; or --CH.sub.2 O--N.dbd.C(R.sup.31)--. PA1 R.sup.1 is methyl; and PA1 R.sup.2 is methyl. PA1 A is N or CR.sup.14 ; PA1 G is N; and PA1 Y is --CH.dbd.CR.sup.6 -C(.dbd.W.sup.1)--A.sup.1 --; or --CH.sub.2 O--N.dbd.C(R.sup.31)--. PA1 R.sup.1 is methyl; and PA1 R.sup.2 is methyl. PA1 [[2-(1,5--dihydro-3-methoxy-1-methyl-5-oxo-4H-1,2,4-triazol-4-yl)phenyl]met hyl] N-(4-chlorophenyl)propanimidothioate; PA1 1,1-dimethylethyl 2-chloro-3-[2-(1,5-dihydro-3-methoxy-1-methyl-5-oxo-4H-1,2,4-triazol4-yl)p henyl]-2-propenoate; PA1 S-methyl 3,4-dichloro-N-[[2-(1,5-dihydro-3-methoxy-1-methyl-5-oxo-4H-1,2,4-triazol- 4-yl)phenyl]methoxy]benzenecarboximidothioate; and PA1 S-methyl N-[[2-(1,5-dihydro-3-methoxy-1-methyl-5-oxo-4H-1,2,4-triazol-4-yl)phenyl]m ethoxy]-3,5-bis(trifluoromethyl)benzenecarboximidothioate.
EP-A-617,014 discloses certain amides and esters of Formula ii as fungicides ##STR3## wherein R.sup.1 is C.sub.1 -C.sub.6 alkyl;
EP-A-656,351, WO 95/18789 and WO 95/21153 also disclose amides and esters similar to those in the above two publications as fungicides.
The cyclic amides of the present invention are not disclosed in any of the above publications.
J. Heterocyclic Chem., (1987), 24, 465, J. Heterocyclic Chem., (1988), 25, 1307, and Australian J. Chem., (1977), 30 (8), 1815 disclose 4-nitrophenyl isoxazoles (iii), phenyl pyrazolones (iv), and aryl isothiazolinones (v) respectively. ##STR4##
However, no utility as fungicides is alleged and the cyclic amides of the present invention are not disclosed therein.